WO2004052076A2 - Mixed esters of dicarboxylic acids for use as pigment dispersants - Google Patents
Mixed esters of dicarboxylic acids for use as pigment dispersants Download PDFInfo
- Publication number
- WO2004052076A2 WO2004052076A2 PCT/US2003/039038 US0339038W WO2004052076A2 WO 2004052076 A2 WO2004052076 A2 WO 2004052076A2 US 0339038 W US0339038 W US 0339038W WO 2004052076 A2 WO2004052076 A2 WO 2004052076A2
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- WO
- WIPO (PCT)
- Prior art keywords
- compound
- carbon atoms
- saturated
- aliphatic moiety
- unsaturated
- Prior art date
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 25
- 239000002270 dispersing agent Substances 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title abstract description 21
- 150000001991 dicarboxylic acids Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 239000000516 sunscreening agent Substances 0.000 claims abstract description 14
- 230000000475 sunscreen effect Effects 0.000 claims abstract description 13
- XXBAQTDVRLRXEV-UHFFFAOYSA-N 3-tetradecoxypropan-1-ol Chemical compound CCCCCCCCCCCCCCOCCCO XXBAQTDVRLRXEV-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 Isostearyl Chemical group 0.000 claims abstract description 11
- 229940116987 ppg-3 myristyl ether Drugs 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- QCEPSBVEYFCCSO-GRVYQHKQSA-N CCCCCCCCOCCCC.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O Chemical compound CCCCCCCCOCCCC.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O QCEPSBVEYFCCSO-GRVYQHKQSA-N 0.000 claims abstract description 6
- 239000003974 emollient agent Substances 0.000 claims description 15
- 230000000699 topical effect Effects 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000004909 Moisturizer Substances 0.000 claims description 4
- 230000001333 moisturizer Effects 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical group CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims 2
- 150000002191 fatty alcohols Chemical class 0.000 abstract description 22
- 239000006185 dispersion Substances 0.000 abstract description 8
- 238000009736 wetting Methods 0.000 abstract description 5
- 239000012530 fluid Substances 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VJZWIFWPGRIJSN-XRHABHTOSA-N dilinoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O VJZWIFWPGRIJSN-XRHABHTOSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940043348 myristyl alcohol Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical class CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 3
- HLKBESQBAMRXPZ-UHFFFAOYSA-N 1-butoxyoctane Chemical compound CCCCCCCCOCCCC HLKBESQBAMRXPZ-UHFFFAOYSA-N 0.000 description 2
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 description 2
- PTPDZZWUOHQSLG-UHFFFAOYSA-N 2-octyldodecyl 2,2-dimethylpropanoate Chemical compound CCCCCCCCCCC(COC(=O)C(C)(C)C)CCCCCCCC PTPDZZWUOHQSLG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940048862 octyldodecyl neopentanoate Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 1
- UIVPNOBLHXUKDX-UHFFFAOYSA-N 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CCOC(=O)CC(C)CC(C)(C)C UIVPNOBLHXUKDX-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GORMSINSWZJIKL-UHFFFAOYSA-N [3-(2-ethylhexanoyloxy)-2,2-dimethylpropyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC(C)(C)COC(=O)C(CC)CCCC GORMSINSWZJIKL-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- IHURUMZMADFAGS-VHXPQNKSSA-N bis(2-octyldodecyl) (Z)-hexatriacont-18-enedioate Chemical compound CCCCCCCCCCC(CCCCCCCC)COC(=O)CCCCCCCCCCCCCCCC\C=C/CCCCCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC IHURUMZMADFAGS-VHXPQNKSSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229960001673 diethyltoluamide Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 229940100554 isononyl isononanoate Drugs 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
Definitions
- the present invention relates to novel mixed esters of polypropoxylated fatty alcohols and monohydric fatty alcohols with dicarboxylic fatty acids. These compounds exhibit unique pigment dispersion, emolliency and gloss-imparting properties.
- the fatty mixed esters of the present invention are particularly useful in the formulation of make-ups and other pigmented products, lotions, lipsticks, cold creams, skin moisturizers, sunscreen lotions, topical pharmaceutical products and cleansing creams.
- the present invention further relates to topical preparations incorporating the fatty mixed esters of the present invention. Background
- a diverse range of formulations useful in personal care and pharmaceutical applications utilize inorganic pigments and other micronized inorganic oxides, such as physical sunscreen ingredients.
- these finely divided particulate products are dispersed within formulations by mixing, using either low-shear or high-shear methods.
- uniform dispersions must be produced, with all particles wetted out and which remain in suspension over a period of time without settling, jelling or agglomerating. Producing such stable suspensions has proved to be a challenge, although some successes have been achieved. For example, U.S.
- Patent 5,116,604 to Foget describes the use of neopentanoate esters, in particular isoarchidyl neopentanoate, as cosmetic emollients for sunscreen products.
- U.S. Patent 5 ,716,602 to Uick describes sunscreens formulated to include a water resistance agent and an insect repellent.
- One formulation has in it an aqueous emulsion DEET, a sunscreen agent, an anionic surfactant, an alkylated PVP, and octyldodecyl neopentanoate. Both Fogel and Uick use
- U. S . Patent 5,476,643 to Fogel describes the use of two specific neopentyl glycol diesters, as wetting, dispersing, spreading and detergent agents for micronized TiO 2 1 ZnO and other pigments. These esters, neopentyl glycol di-2-ethyl hexanoate andneopentyl glycol di-isostearate, are used in varying combinations and may also be used with an emulsifying agent for a water dispersible pigmented make-up cleaner composition.
- Emollients such as C ⁇ 2 -C 15 Alkyl Benzoate (Finsolv TN, Finetex, Inc.) and Tridecyl : Neopentanoate (TPJVENT NP-13 ) have also been employed with some success as dispersahts for physical sunscreens, as have various glycols andpropoxylates, such as PPG-3 Myristyl Ether. See for example, U.S. Patent 5,928,631 to Lucas which describes a skin composition for controlling environmental malodors on the body.
- the composition comprises from about 0.1% to about 5%, by weight of a solubilized, water-soluble, uncomplexed cyclodextrin; from about 0.1% to about 36%, by weight of an oil phase selected from the group consisting of emollients, moisturizers, and skin protectants; one or more surfactants, and an aqueous carrier.
- a solubilized, water-soluble, uncomplexed cyclodextrin from about 0.1% to about 36%, by weight of an oil phase selected from the group consisting of emollients, moisturizers, and skin protectants; one or more surfactants, and an aqueous carrier.
- 5,302,377 to Periera. et al. discloses a fatty alkoxylated ester of tricarboxylic acid and a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols with emollient properties for topical preparations.
- the preparations include mineral oil as a second emollient.
- 5,455,025 to Pereira. et al. discloses fatty alkoxylated esters of tricarboxylic acid with a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols having emollient properties for topical preparations.
- novel compounds of this invention have the following structural formula:
- R has the structural formula:
- R is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety containing from 4 to 24 carbon atoms;
- X is an integer from 3 to 30;
- R 2 is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety which contains from 4 to 40 carbon atoms;
- R 3 is a saturated or unsaturated, straight chain or branched chain aliphatic moiety containing from 12 to 24 carbon atoms.
- the preferred compounds are Octyldodecyl PPG-3 Myristyl Ether Dilinoleate and Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
- novel compounds of this invention are particularly useful in wetting and dispersing pigments, including such pigments as metallic oxides.
- the novel mixed esters of this invention are produced by the reaction of propoxylated fatty alcohols and monohydric fatty alcohols with dicarboxylic fatty acids.
- the propoxylated fatty alcohols have a carbon chain length between 4 and 24 carbon atoms and a degree of propoxylation between 3 and 30, and most preferably between 3 and 15 units of propylene oxide.
- the diacid used in this invention is an aliphatic diacid having a carbon chain length between 4 and 40.
- the preferred fatty alcohols are chosen from a group having a carbon chain length between 12 and 24.
- a preferred aliphatic diacid is dilinoleic acid and preferred propoxylated fatty alcohols are myristyl alcohol and butyloctanol.
- Preferred monohydric fatty alcohols are oetyldodecanol and isostearyl alcohol.
- the highly preferred compounds are Octyldodecyl PPG-3 Myristyl Ether Dilinoleate and Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
- Topical formulations which include the aforedescribed mixed esters, one or more active ingredients, and water.
- Suitable active ingredients for use in such topical preparations include organic sunscreens, physical sunscreens, self-tanning agents, pigments, opacifying agents, moisturizers, film-formers, thickening agents, emulsifiers, antiseptic agents, conditioning agents and deodorant actives.
- topical preparations in addition to including the aforedescribed mixed esters of fatty polypropoxylated esters, may also include one or more active ingredients, water and an optional second emollient agent, and fragrances, humectants, protein derivatives, coloring agents, preservatives and the like as well.
- Preferred topical formulations in accordance with the present invention include the aforedescribed fatty mixed polypropoxylated diesters, either alone or in combination with a second emollient agent, in a range of from about 0.2% to about 20.0% by weight of the composition.
- the second emollient agent when present, may be blended, with the compounds of this invention in a ratio of about 3 : 1 by weight of the former to the latter.
- the fatty alcohol e.g., myristyl alcohol
- propylene oxide in the presence of an alkaline catalyst in a manner well known in the art, followed. by neutralization with a suitable acid such as phosphoric acid.
- a suitable acid such as phosphoric acid.
- Either one or two equivalents of the resultant propoxylated fatty alcohol (e.g., PPG-3 Myristyl ether) and one or two equivalents of the monohydric fatty alcohol (e.g. oetyldodecanol) are reacted in the conventional fashion with one mole of the dicarboxylic acid (e.g., dilinoleic acid).
- a suitable base such as sodium carbonate.
- the typical reaction is as follows:
- a four-neck flask was charged with 3 moles (1 ,254 grams) of the PPG-4 Butyloctyl Ether; 3 moles of Isostearyl Alcohol (840 grams), along with 3 moles (1,755 grams) of Dilinoleic Acid.
Abstract
Novel mixed esters of dicarboxylic acids with monohydric fatty alcohols and propoxylated pigments used in foundations, make-ups, lipsticks and physical sunscreens. The compounds of the present invention show superior pigment wetting and dispersing properties, as demonstrated by their ability to form fluid, very high-solids dispersions, while exhibiting unusual emolliency and gloss formation. The novel compounds of this invention have the structural formula (I), wherein R1 is as the structural formula (II), wherein: R4 is a saturated or unsaturated, substituted or unsubstituted moiety containing from 4 to 24 carbon atoms; X is an integer from 3 to 30; R2 is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety which contains from 4 to 40 carbon atoms; and R3 is a saturated or unsaturated, straight or branched chain aliphatic moiety containing from 12 to 24 carbon atoms. The preferred compounds are Octyldodecyl PPG-3 Myristyl Ether Dilinoleate and Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
Description
Title: MIXED ESTERS OF DICARBOXYLIC ACIDS FOR USE AS PIGMENT DISPERSANTS
SPECIFICATION Related Applications This application claims the priority ofProvisional Application Serial No.60/431,758 filed
December 09, 2002, the entire disclosure of which is incorporated herein by reference. Field of the Invention
The present invention relates to novel mixed esters of polypropoxylated fatty alcohols and monohydric fatty alcohols with dicarboxylic fatty acids. These compounds exhibit unique pigment dispersion, emolliency and gloss-imparting properties. The fatty mixed esters of the present invention are particularly useful in the formulation of make-ups and other pigmented products, lotions, lipsticks, cold creams, skin moisturizers, sunscreen lotions, topical pharmaceutical products and cleansing creams. The present invention further relates to topical preparations incorporating the fatty mixed esters of the present invention. Background
A diverse range of formulations useful in personal care and pharmaceutical applications utilize inorganic pigments and other micronized inorganic oxides, such as physical sunscreen ingredients. Typically, these finely divided particulate products are dispersed within formulations by mixing, using either low-shear or high-shear methods. In order to make stable, cosmetically acceptable products, uniform dispersions must be produced, with all particles wetted out and which remain in suspension over a period of time without settling, jelling or agglomerating. Producing such stable suspensions has proved to be a challenge, although some successes have been achieved.
For example, U.S. Patent 5,116,604 to Foget describes the use of neopentanoate esters, in particular isoarchidyl neopentanoate, as cosmetic emollients for sunscreen products. U.S. Patent 5 ,716,602 to Uick describes sunscreens formulated to include a water resistance agent and an insect repellent. One formulation has in it an aqueous emulsion DEET, a sunscreen agent, an anionic surfactant, an alkylated PVP, and octyldodecyl neopentanoate. Both Fogel and Uick use
Octyldodecyl Neopentanoate.
U. S . Patent 5,476,643 to Fogel describes the use of two specific neopentyl glycol diesters, as wetting, dispersing, spreading and detergent agents for micronized TiO2 1 ZnO and other pigments. These esters, neopentyl glycol di-2-ethyl hexanoate andneopentyl glycol di-isostearate, are used in varying combinations and may also be used with an emulsifying agent for a water dispersible pigmented make-up cleaner composition.
Emollients such as Cι2-C15 Alkyl Benzoate (Finsolv TN, Finetex, Inc.) and Tridecyl : Neopentanoate (TPJVENT NP-13 ) have also been employed with some success as dispersahts for physical sunscreens, as have various glycols andpropoxylates, such as PPG-3 Myristyl Ether. See for example, U.S. Patent 5,928,631 to Lucas which describes a skin composition for controlling environmental malodors on the body. The composition comprises from about 0.1% to about 5%, by weight of a solubilized, water-soluble, uncomplexed cyclodextrin; from about 0.1% to about 36%, by weight of an oil phase selected from the group consisting of emollients, moisturizers, and skin protectants; one or more surfactants, and an aqueous carrier. ' Several other possibly relevant US Patents are:
4,830,768 to Reich, et al. discloses a fatty propoxylated ester of dicarboxylic acid and fatty alcohol with 1-15 units of propoxylation. Lubricating properties are claimed for non-topical preparations.
5,693,316 to Pereira. et al. discloses a fatty alkoxylated ester of dicarboxylic acid and a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols with emollient properties for topical preparations. The preparations include mineral oil as a second emollient.
5,302,377 to Periera. et al. discloses a fatty alkoxylated ester of tricarboxylic acid and a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols with emollient properties for topical preparations. The preparations include mineral oil as a second emollient. 5,455,025 to Pereira. et al. discloses fatty alkoxylated esters of tricarboxylic acid with a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols having emollient properties
for topical preparations.
5,597,555 to Pereira. et al. discloses a fatty alkoxylated ester of dicarboxylic acid with a stoichiometric excess of 1 or more polyalkoxylated fatty alcohols with emollient properties for topical preparations.. 6,476,254 to Pereira. et al. discloses a fatty alkoxylated ester of dicarboxylic acid and fatty alcohol with pigment wetting/dispersant/emollient properties for topical preparations.^
None of these references disclose mixed fatty acid esters of dicarboxylic acid and their use as effective'pigment dispersants.
Thus there remains a need for superior dispersants with desirable esthetic properties for use in pigmented cosmetic compositions, particularly sunscreen formulations that contain physical sunscreens.
Additionally, since formulators often find it useful to fully disperse pigments, e.g.,' micronized metallic oxides, in a portion of the oil phase by high shear techniques such as milling, there is a need for forming oil phase dispersions which have a high solids content of pigments, particularly micronized metallic oxides, that are fluid.
Summary of the Invention
We have now discovered that certain novel mixed esters produced by reacting dicarboxylic acids with monohydric fatty alcohols and propoxylated fatty alcohols show unusual, unexpectedly superior properties as pigment dispersants, especially for inorganic pigments used in foundations, make-ups, lipsticks and physical sunscreens. The compounds of the present invention show superior pigment wetting and dispersing properties, as demonstrated by their ability to form fluid, very high-solids dispersions, while exhibiting unusual emolliency and gloss formation.
The novel compounds of this invention have the following structural formula:
o o il I! ] -0- C- 2-C- 0- 3
wherein R, has the structural formula:
CH3
-(0 -CH -CH2) x~ O -R4
wherein:
R, is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety containing from 4 to 24 carbon atoms;
X is an integer from 3 to 30; R2 is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety which contains from 4 to 40 carbon atoms; and
R3 is a saturated or unsaturated, straight chain or branched chain aliphatic moiety containing from 12 to 24 carbon atoms.
The preferred compounds are Octyldodecyl PPG-3 Myristyl Ether Dilinoleate and Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
Detailed Description of nvention
The novel compounds of this invention are particularly useful in wetting and dispersing pigments, including such pigments as metallic oxides. The novel mixed esters of this invention are produced by the reaction of propoxylated fatty alcohols and monohydric fatty alcohols with dicarboxylic fatty acids. Preferably, the propoxylated fatty alcohols have a carbon chain length between 4 and 24 carbon atoms and a degree of propoxylation between 3 and 30, and most preferably between 3 and 15 units of propylene oxide.
It is additionally preferred that the diacid used in this invention is an aliphatic diacid having a carbon chain length between 4 and 40. The preferred fatty alcohols are chosen from a group having a carbon chain length between 12 and 24.
A preferred aliphatic diacid is dilinoleic acid and preferred propoxylated fatty alcohols are myristyl alcohol and butyloctanol. Preferred monohydric fatty alcohols are oetyldodecanol and isostearyl alcohol.
The highly preferred compounds are Octyldodecyl PPG-3 Myristyl Ether Dilinoleate and Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
This invention is also directed to topical formulations which include the aforedescribed mixed esters, one or more active ingredients, and water. A second emollient agent of mineral oil, petrolatum and the like, may also be included. Suitable active ingredients for use in such topical preparations include organic sunscreens, physical sunscreens, self-tanning agents, pigments, opacifying agents, moisturizers, film-formers, thickening agents, emulsifiers, antiseptic agents, conditioning agents and deodorant actives.
These aforedescribed topical preparations, in addition to including the aforedescribed mixed esters of fatty polypropoxylated esters, may also include one or more active ingredients, water and an optional second emollient agent, and fragrances, humectants, protein derivatives, coloring agents, preservatives and the like as well. Preferred topical formulations in accordance with the present invention include the aforedescribed fatty mixed polypropoxylated diesters, either alone or in combination with a second emollient agent, in a range of from about 0.2% to about 20.0% by weight of the composition. The second emollient agent, when present, may be blended, with the compounds of this invention in a ratio of about 3 : 1 by weight of the former to the latter. Examples of Preparation of the Compounds
The fatty alcohol, e.g., myristyl alcohol, is reacted with propylene oxide in the presence of an alkaline catalyst in a manner well known in the art, followed. by neutralization with a suitable acid such as phosphoric acid. Either one or two equivalents of the resultant propoxylated fatty alcohol (e.g., PPG-3 Myristyl ether) and one or two equivalents of the monohydric fatty alcohol (e.g. oetyldodecanol) are reacted in the conventional fashion with one mole of the dicarboxylic acid (e.g., dilinoleic acid). This is followed by neutralization with a suitable base such as sodium carbonate. The typical reaction is as follows:
(3) CH3CH2CH2 + CH3 (CH2)]2 CH2 OH -> CH3CCH2)]2CH2(0CHCH2)3OH
O! " C ' H3
(propylene oxide) (myrlsty! alcohol) (PPG-3 myrlsryi ether)
O O
I I I I
CH3(CH2)]2CH2(OCHCH2)3θH + CHs(CH2)oCHCH2θH + OH-C-(CH34H62) -C-OH->
I 1
CH3 ' CH3(CH2)όCH?.
(PPG-3 myristyl ether) (octyJdαtiecαnoø (dlllnotølc add)
O O
I I I I
CH3CH2(CH2)l2CH2COCHCHCH2)3θ-C-C34Hό2-C-OCH2CH(CH2)9CH3
1 I
CH3 CH3(CH2)όCH2
(Octyldodecyl PPG-3 Myristyl Ether Dilinoleate)
Preparation of Octyldodecyl PPG-3 Myristyl Ether Dilinoleate
3 moles (642 grams) of Myristyl Alcohol were charged to an autoclave, and 0.1% of Potassium Hydroxide was added as a catalyst. The autoclave was purged with Nitrogen and 9 moles (522 grams) of Propylene Oxide were added at a temperature of 150-160°C and a pressure of 30-40 psi. At the completion of the addition reaction, the batch was cooled to 80°C and neutralized with Phosphoric Acid. The resultant 1 , 164 grams of product, PPG-3 Myristyl Ether, a pale yellow liquid, was charged to a four-neck flask.
Three (3) moles (900 grams) of Oetyldodecanol and Dilinoleic Acid were charged to the flask, along with a catalytic amount of methanesulfonic acid. The reaction mixture was heated with agitation to 150°C under 28" Hg of vacuum until an acid value of less than 5 mg KOH was obtained. The reaction mixture was cooled to 80°C, washed with a dilute Sodium Carbonate solution sufficient to neutralize the residual acid present, followed by washing with water.
The ester layer was separated and heated under vacuum until a moisture content of less than 0.3% was obtained, followed by vacuum filtration. The resultant product, Octyldodecyl PPG-3 Myristyl Ether Dilinoleate, was a clear pale yellow liquid having an acid value of 0.32 mg KOH. 5 Preparation of Isostearyl PPG-4 Butyloctyl Ether Dilinoleate
4 moles (744 grams) of Butyloctanol were charged to an autoclave, and 0.1% of Potassium
Hydroxide was added as catalyst. The autoclave was purged with Nitrogen and 16 moles (928 grams) of Propylene Oxide were added at a temperature of 150-160°C and a pressure of 30-40 psi. Upon completion, the batch was cooled to 80°C and neutralized with Phosphoric Acid. The
10 resultant product, PPG-4 Butyloctyl Ether, was a very pale yellow liquid.
A four-neck flask was charged with 3 moles (1 ,254 grams) of the PPG-4 Butyloctyl Ether; 3 moles of Isostearyl Alcohol (840 grams), along with 3 moles (1,755 grams) of Dilinoleic Acid.
A catalytic' amount of p-Toluenesulfonic Acid was added and the reaction mixture was heated with agitation to 140°C under 28" Hg of vacuum until an acid value of less than 5 mg 15. KOH was obtained. The reaction mixture was cooled to 80°C, washed with a dilute Sodium Hydroxide solution sufficient to neutralize the residual acid present, followed by washing with water. The ester layer was separated and heated under vacuum until a moisture content of less than 0.2% was obtained, followed by vacuum filtration. The resultant product, Isostearyl PPG-4 Butyloctyl Ether Dilinoleate, was a clear very pale yellow liquid having an acid value of less than 20 0.1 mg KOH.
Compaative Examples
Comparisons were made between the compounds of the present invention and several common dispersants used in foundations and lipsticks for their ability for form fluid, high-solids dispersions.
25 The tests were performed by adding 10 grams of yellow iron oxide to 90 grams of the test dispersant in a beaker and mixing for 15 minutes with a Silverson mixer at 9,000 rpm. After 15 minutes, the sample was checked with a grind gauge to confirm full dispersion. The dispersion was cooled to room temperature and the viscosity was measured. Additional 2-gram increments of pigment were added, following the above procedure, until streaking was observed with the 0 grind gauge or until a viscosity of 10,000 cps was reached. a) With mineral oil the cut-off viscosity was exceeded at 10 grams of pigment.
b) With C12-C15 Alkyl Benzoate the cut-off viscosity was reached at about 11 grams of pigment. c) With Isononyl Isononanoate the cut-off viscosity was reached at about 16 grams of pigment. d)With castor oil the cut-off viscosity was reached at about 21 grams of pigment. e) With Cyclomethicone the cut-off viscosity was reached at about 26 grams of pigment. f) With Dioctyldodecyl Dimer Dilinoleate the cut-off viscosity was reached at about 34 grams of pigment: g) With Octyldodecyl PPG-3 Myristyl Ether Dimer Dilinoleate the addition of about 66 grams of pigment remained below the cut-off viscosity, which measured at approximately
6,000 cps. '
These comparisons demonstrate that a mixed ester of a dicarboxylic acid with a fatty alcohol and a propoxylated fatty alcohol exhibit unusual pigment dispersant properties.
Claims
1. A compound of the following structural formula:
o o i! Ii
R1 -O- C- R2-C-O- R3
wherein Rj has the formula:
CH3
,-CO-CH-CH2)x- 0-R
wherein: ^s a saturated or unsaturated, substituted or unsubstituted aliphatic moiety containing from 4 to 24 carbon atoms;
X is an integer from 3 to 30;
R2 is a saturated or unsaturated, substituted or unsubstituted aliphatic moiety which contains from 4 to 40 carbon atoms; and
R3 is a saturated or unsaturated, straight chain or branched chain aliphatic moiety containing from 12 to 24 carbon atoms.
2. The compound of claim 1 where R, is a saturated aliphatic moiety containing from 4 to 24 carbon atoms.
3. The compound of claim 1 where R4 is a saturated aliphatic moiety of 12 or 20
carbon atoms.
4. The compound of claim 1 , wherein R2 is a saturated aliphatic moiety which contains from 4 to 40 carbon atoms.
5. The compound of claim 1 , where R2 is a saturated aliphatic moiety which contains 34 carbon atoms.
6. The compound of claim 1 , where X is from 3 to 30.
7. The compound of claim 1 , where X is 3 or 4.-
8. The compound of claim 1 wherein R3 is a saturated, branched chain aliphatic moiety containing from 12 to.24 carbon atoms.
9. The compound of claim 1 wherein R3 is a saturated branched chain aliphatic moiety which contains 12 or 20 carbon atoms.
10. The compound of claim 1 , wherein R3 is Octyldodecane.
11. The compound of claim 1, wherein R3 is Isostearyl.
12. The compound Octyldodecyl PPG-3 Myristyl Ether Dilinoleate.
13. The compound Isostearyl PPG-4 Butyloctyl Ether Dilinoleate.
14. A topical composition for topical application comprising an effective amount of an active ingredient dispersed in the topical composition, the active ingredient selected from the group consisting of pigments, micronized physical sunscreen, organic sunscreens, self-tanning agents, opacifying agents, antiseptic agents, moisturizers, film-formers, deodorant actives, emulsifiers, thickening agents, and a dispersant emollient agent in sufficient amount to disperse such active ingredient, such agent being a compound of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03812882.3A EP1575532B1 (en) | 2002-12-09 | 2003-12-08 | Mixed esters of dicarboxylic acids for use as pigment dispersants |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43175802P | 2002-12-09 | 2002-12-09 | |
| US60/431,758 | 2002-12-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2004052076A2 true WO2004052076A2 (en) | 2004-06-24 |
| WO2004052076A3 WO2004052076A3 (en) | 2004-09-02 |
Family
ID=32507793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2003/039038 WO2004052076A2 (en) | 2002-12-09 | 2003-12-08 | Mixed esters of dicarboxylic acids for use as pigment dispersants |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US7015350B2 (en) |
| EP (1) | EP1575532B1 (en) |
| WO (1) | WO2004052076A2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1676565A1 (en) * | 2004-12-30 | 2006-07-05 | L'oreal | Cosmetic composition comprising an ester of an alcoxylated alcohol and a film-forming polymer |
| EP1676564A1 (en) | 2004-12-30 | 2006-07-05 | L'oreal | Cosmetic composition containing an ester of alkoxylated alcohol and a non polar oil |
| FR2880264A1 (en) * | 2004-12-30 | 2006-07-07 | Oreal | Cosmetic composition, useful as e.g. hair care or make up product, comprises an alkoxy alcohol, carboxylic acid ester and a hydrocarbon ester |
| WO2012113716A2 (en) | 2011-02-25 | 2012-08-30 | L'oreal | Cosmetic compositions having long lasting shine |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060171910A1 (en) * | 2004-12-30 | 2006-08-03 | Audrey Ricard | Cosmetic composition containing an alkoxylated alcohol ester and a hydrocarbon-based ester oil |
| US7673687B2 (en) * | 2007-12-05 | 2010-03-09 | Halliburton Energy Services, Inc. | Cement compositions comprising crystalline organic materials and methods of using same |
| AU2011250962B2 (en) | 2010-05-10 | 2015-09-03 | Gfbiochemicals Limited | Personal care formulations containing alkyl ketal esters and methods of manufacture |
| WO2012021826A2 (en) | 2010-08-12 | 2012-02-16 | Segetis, Inc. | Latex coating compositions including carboxy ester ketal coalescents, methods of manufacture, and uses thereof |
| WO2014047428A1 (en) | 2012-09-21 | 2014-03-27 | Segetis, Inc. | Cleaning, surfactant, and personal care compositions |
| AU2013352172A1 (en) | 2012-11-29 | 2015-06-11 | Gfbiochemicals Limited | Carboxy ester ketals, methods of manufacture, and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830768A (en) * | 1988-02-22 | 1989-05-16 | Aluminum Company Of America | Metalworking lubricant composition containing propoxylated fatty alcohol |
| US5116604A (en) * | 1991-01-16 | 1992-05-26 | Bernel Chemical Co. | Sunscreen compositions containing novel neopentanoate esters |
| US5928631A (en) * | 1997-06-09 | 1999-07-27 | The Procter & Gamble Company | Methods for controlling environmental odors on the body using compositions comprising uncomplexed cyclodextrins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725432A (en) | 1983-01-26 | 1988-02-16 | The Procter & Gamble Company | Antiperspirant and deodorant stick composition |
| US5302377A (en) | 1992-04-02 | 1994-04-12 | Croda, Inc. | Fatty alkoxylate esters of aliphatic and aromatic dicarboxylic and tricarboxylic acids as emollients |
| US5597555A (en) | 1992-04-02 | 1997-01-28 | Croda, Inc. | Fatty alkoxylate esters of aliphatic and aromatic dicarboxylic acids |
| US5455025A (en) | 1992-04-02 | 1995-10-03 | Croda, Inc. | Non-aqueous emollient compositions for topical application |
| US5476643A (en) | 1993-11-19 | 1995-12-19 | Bernel Chemical Co. | Method of dispersing micronized TIo2, ZnO and other pigments |
| US6623744B2 (en) | 1995-06-22 | 2003-09-23 | 3M Innovative Properties Company | Stable hydroalcoholic compositions |
| US5716602A (en) | 1996-06-26 | 1998-02-10 | S. C. Johnson & Sons, Inc. | Insect repellent sunscreen |
| FR2776509B1 (en) * | 1998-03-31 | 2001-08-10 | Oreal | TOPICAL COMPOSITION CONTAINING AN ESTER OF FATTY ACID OR ALCOHOL BRANCHED IN C24 TO C28 |
| JP2003523928A (en) * | 1998-10-02 | 2003-08-12 | クローダ，インコーポレイテッド | Alkoxylated fatty alcohol dicarboxylates |
| US6511952B1 (en) | 2000-06-12 | 2003-01-28 | Arco Chemical Technology, L.P. | Use of 2-methyl-1, 3-propanediol and polycarboxylate builders in laundry detergents |
| WO2003024416A1 (en) | 2001-03-02 | 2003-03-27 | Innovachem, Inc. | Monocarboxylic acid esters of propoxylated fatty alcohols as pigment dispersants |
| WO2003013439A2 (en) | 2001-08-09 | 2003-02-20 | Croda, Inc. | Anti-irritants |
-
2003
- 2003-12-08 US US10/730,752 patent/US7015350B2/en not_active Expired - Lifetime
- 2003-12-08 WO PCT/US2003/039038 patent/WO2004052076A2/en not_active Application Discontinuation
- 2003-12-08 EP EP03812882.3A patent/EP1575532B1/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830768A (en) * | 1988-02-22 | 1989-05-16 | Aluminum Company Of America | Metalworking lubricant composition containing propoxylated fatty alcohol |
| US5116604A (en) * | 1991-01-16 | 1992-05-26 | Bernel Chemical Co. | Sunscreen compositions containing novel neopentanoate esters |
| US5928631A (en) * | 1997-06-09 | 1999-07-27 | The Procter & Gamble Company | Methods for controlling environmental odors on the body using compositions comprising uncomplexed cyclodextrins |
Non-Patent Citations (1)
| Title |
|---|
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1676565A1 (en) * | 2004-12-30 | 2006-07-05 | L'oreal | Cosmetic composition comprising an ester of an alcoxylated alcohol and a film-forming polymer |
| EP1676564A1 (en) | 2004-12-30 | 2006-07-05 | L'oreal | Cosmetic composition containing an ester of alkoxylated alcohol and a non polar oil |
| FR2880264A1 (en) * | 2004-12-30 | 2006-07-07 | Oreal | Cosmetic composition, useful as e.g. hair care or make up product, comprises an alkoxy alcohol, carboxylic acid ester and a hydrocarbon ester |
| FR2880263A1 (en) * | 2004-12-30 | 2006-07-07 | Oreal | COSMETIC COMPOSITION CONTAINING ALKOXYL ALCOHOL ESTER AND APOLAR OIL |
| EP1683513A1 (en) | 2004-12-30 | 2006-07-26 | L'oreal | Cosmetic composition comprising an ester of an alcoxylated alcohol and a hydrocarbon ester oil |
| WO2012113716A2 (en) | 2011-02-25 | 2012-08-30 | L'oreal | Cosmetic compositions having long lasting shine |
Also Published As
| Publication number | Publication date |
|---|---|
| US7015350B2 (en) | 2006-03-21 |
| EP1575532A2 (en) | 2005-09-21 |
| EP1575532B1 (en) | 2016-07-20 |
| US20040147602A1 (en) | 2004-07-29 |
| EP1575532A4 (en) | 2009-01-14 |
| WO2004052076A3 (en) | 2004-09-02 |
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